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    Business Insurance Account Executive

    Gusto

    Remote
    Financial
    Hybrid
    See your match score
    Posted 1 week ago
    Work Type

    On-site

    Vertical

    Financial

    Source

    jobscollider

    About this role

    About Gusto

    At Gusto, we’re on a mission to grow the small business economy. We handle the hard stuff — payroll, health insurance, 401(k)s, and HR — so owners can focus on their craft and their customers. With teams in Denver, San Francisco, and New York, we support more than 500,000 small businesses nationwide and are building a workplace that reflects the people we serve.

    All full-time employees receive competitive base pay,

    benefits, and equity (RSUs) — because everyone who helps build Gusto should share in its success. Offer amounts are determined by role, level, and location. Learn more about our Total Rewards philosophy.

    AI is a fundamental part of how work gets done at Gusto. We expect all team members to actively engage with AI tools relevant to their role and grow their fluency as the technology evolves. AI experience

    requirements vary by role and will be assessed during the interview process.

    About the Role:

    We are seeking a highly motivated and licensed Property & Casualty (P&C) Insurance Broker to join our team as part of a critical pilot to launch a P&C broker model at Gusto. You will be essential in evolving Gusto’s business insurance channel by acting as a licensed agent to quote and issue business insurance policies with our NEXT Insurance carrier partner.

    You will use your expertise to provide direct support and an improved experience for small business customers with complex insurance needs, helping to capture meaningfully higher revenue and accelerating the development of our AI Insurance Advisor.

    About the Team:

    This team is crucial to solving customer experience gaps and optimizing our offline insurance channels. You will be a SME who is part of the “human-in-the-loop” workflows required to train and optimize Gus as an AI insurance advisor. Our collective vision is to be an expert advisor that supports small businesses through every stage of growth, with this pilot being key to establishing our digita

    Commission Structure

    Base Salary

    $,k

    Commission

    Structure not specified

    Ramp Period

    Not mentioned — clarify timeline

    Accelerators

    Yes

    Selling Motion

    Prospecting

    Channel / Partner

    Sell through partners, resellers, or alliances

    Requirements at a Glance

    Bachelor's Degree·Required

    Typical Day — Account Executive

    Stakeholder meetings3–5/week
    Executive presentations2–3/week
    Business cases & RFPs1–2/week
    Forecast & pipeline2×/week
    Champion coachingDaily

    Estimates based on role type and selling motion — actual may vary by company.

    Role Signals

    Green Flags

    ✓
    Equity/Stock Options

    Ownership stake offered

    Financial Services — Interview Intel

    Typical Sales Cycle

    3–6 months (Retail) · 6–18 months (Institutional)

    Common Buyer Objections

    • "Regulatory concerns — need compliance approval"
    • "We already have a vendor for this"
    • "Need to see 3-year track record"
    • "Committee-based decision — multiple approvers"

    Key Industry Metrics

    AUM (Assets Under Management)Risk-Adjusted ReturnsCompliance Pass RateClient Retention RateRevenue Per Advisor

    Hot Topics to Reference

    • • AI in fraud detection and compliance
    • • Open banking APIs
    • • ESG investing mandate shifts
    • • Embedded finance partnerships

    Use these insights to speak the buyer's language in interviews.

    Tags

    sales
    —

    Walk me through your discovery process.

    Template question
    —

    How do you handle a prospect who goes silent mid-deal?

    Template question
    —

    Tell me about your largest closed deal and the sales cycle.

    Template question
    —

    How do you build business cases for stakeholders?

    Template question
    —

    Describe a deal you lost and what you learned.

    Template question
    Research Gusto's product, recent news, and key competitors
    Review relevant certifications and licensing requirements
    Review the job description and map your experience to each requirement
    Role Insights

    As an Account Executive with Gusto, you'll own the entire revenue pipeline and be measured on quota attainment.

    Trust-building is paramount — prospects need confidence in your expertise.

    Are you a closer?

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